Sugar-induced color and orientation changes in a cyanine dye bound to boronic -acid-appended poly(L-lysine)

Taro Kimura, Masayuki Takeuchi, Takeshi Nagasaki, Seiji Shinkai

Research output: Contribution to journalArticle

26 Citations (Scopus)

Abstract

A cyanine dye (2) can be orientated on boronic-acid-modified poly(L- and D-lysine)s (L- and D-1, respectively) in the presence of saccharides. The main driving-force for the association is the electrostatic attraction between cationic 2 and the anionic center developed by complexation of the boronic acid residue with saccharides. The chiral orientation can be monitored by a CD spectroscopic method: it is mainly governed by the chirality of 1 but not by the chirality of saccharides. This is a novel system to control the dye orientation which occurs owing to the cooperative action of both naturally-originated α-amino acids and saccharides.

Original languageEnglish
Pages (from-to)559-562
Number of pages4
JournalTetrahedron Letters
Volume36
Issue number4
DOIs
Publication statusPublished - Jan 23 1995

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Boronic Acids
Chirality
Sugars
Lysine
Coloring Agents
Color
Complexation
Static Electricity
Electrostatics
Association reactions
Amino Acids
cyanine dye 2

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

Sugar-induced color and orientation changes in a cyanine dye bound to boronic -acid-appended poly(L-lysine). / Kimura, Taro; Takeuchi, Masayuki; Nagasaki, Takeshi; Shinkai, Seiji.

In: Tetrahedron Letters, Vol. 36, No. 4, 23.01.1995, p. 559-562.

Research output: Contribution to journalArticle

Kimura, Taro ; Takeuchi, Masayuki ; Nagasaki, Takeshi ; Shinkai, Seiji. / Sugar-induced color and orientation changes in a cyanine dye bound to boronic -acid-appended poly(L-lysine). In: Tetrahedron Letters. 1995 ; Vol. 36, No. 4. pp. 559-562.
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